ANTI-MICHAEL ADDITION OF CYANOCUPRATE TBUCU(CN)LI TO ACCEPTOR-SUBSTITUTED ENYNES

被引:14
作者
GEROLD, A [1 ]
KRAUSE, N [1 ]
机构
[1] TH DARMSTADT,INST ORGAN CHEM,PETERSENSTR 22,D-64287 DARMSTADT,GERMANY
关键词
CUPRATES; ORGANOMETALLIC; ENYNES; ACCEPTOR-SUBSTITUTED; ADDITION; REGIOSELECTIVITY OF; ANTI-MICHAEL ADDITION; PROTONATION;
D O I
10.1002/cber.19941270833
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Acceptor-substituted enynes 1 react with lithium tert-butylcyanocuprate [tBuCu(CN)Li] in THF to afford anti-Michael adducts 3. The formation of the isomeric side products 4 can be suppressed by regioselective protonation of the organometallic intermediates with ethanol at -80-degrees-C. Evidence for radical intermediates or electron-transfer steps in these reactions could not be obtained.
引用
收藏
页码:1547 / 1549
页数:3
相关论文
共 20 条
  • [1] ALLENYL ENOLATES - A NEW CLASS OF CHIRAL AMBIDENT NUCLEOPHILES .1. REACTION WITH C-ELECTROPHILES AND SI-ELECTROPHILES
    ARNDT, S
    HANDKE, G
    KRAUSE, N
    [J]. CHEMISCHE BERICHTE-RECUEIL, 1993, 126 (01): : 251 - 259
  • [2] ORGANOCOPPER-IODOSILANE COMBINATIONS IN CONJUGATE ADDITIONS
    BERGDAHL, M
    LINDSTEDT, EL
    NILSSON, M
    OLSSON, T
    [J]. TETRAHEDRON, 1989, 45 (02) : 535 - 543
  • [3] BORONOEVA TR, 1974, ZH OBSHCH KHIM+, V44, P1949
  • [4] BORONOEVA TR, 1974, J GEN CHEM USSR, V44, P1914
  • [5] 1,3-ADDITION OF TERT-BUTYLMAGNESIUM CHLORIDE TO ETHYL CINNAMATE - UNPRECEDENTED COURSE OF REACTION
    CROSSLAND, I
    [J]. ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1975, 29 (04): : 468 - 470
  • [6] DIASTEREOSELECTIVE 1,6-ADDITION REACTIONS OF ORGANOCUPRATES TO CHIRAL 5-ALKYNYLIDENE-1,3-DIOXAN-4-ONES
    HANDKE, G
    KRAUSE, N
    [J]. TETRAHEDRON LETTERS, 1993, 34 (38) : 6037 - 6040
  • [7] HANDKE G, 1993, THESIS TH DARMSTADT
  • [8] FREE-RADICALS IN THE REACTION OF TERT-BUTYLMAGNESIUM CHLORIDE WITH ETHYL CINNAMATE
    HOLM, T
    CROSSLAND, I
    MADSEN, JO
    [J]. ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1978, 32 (10): : 754 - 758
  • [9] ANTI-MICHAEL CARBOLITHIATION OF SILICON AND PHENYL-SUBSTITUTED ALPHA,BETA-UNSATURATED SECONDARY AMIDES
    KLUMPP, GW
    MIEROP, AJC
    VRIELINK, JJ
    BRUGMAN, A
    SCHAKEL, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (23) : 6740 - 6742
  • [10] KRAUSE N, 1993, LIEBIGS ANN CHEM, P521